My first day at Heavy.com was a Monday in June 2007. That first night we took our clients from MEC to the Bohemian Beer Garden in Queens and played drinking games until everyone was shitfaced. The next night we took a different ad agency and did it again.
It was June. The weather was perfect. I was 22, and on the way home to Morningside Heights I watched the sky change colors over the Queensboro Bridge.
Heavy was video online before YouTube. People came to see what the latest funny, viral video was. We ran some original content and syndicated a lot of other people’s, and most of that was crappy.
On Fridays somebody ordered a lot of beer, and by 2 p.m. everybody was drinking. The office had a tiny balcony off one window. It was part of the architecture, not a place you’d stand to enjoy anything. We went out there anyway to roll spliffs and look at the traffic on 38th street.
It was a toxic workplace, and I didn’t know that.
Here’s what I actually did all day. I made media plans. A media plan is a spreadsheet that tells a client which sites will run their ads, when, and for how much. I made a bazillion of them.
A friend from Columbia had taught me Excel 101. The job made me really, really good at it.
Being good at Excel got me into data analysis. Data analysis got me into building everything. Now I have LUCID.
I was laid off in 2008, after the economy crashed. A couple of weeks before, my grandmother had died.
I was unemployed for a summer, and it turned out to be awesome. Then I got another job.
I’m telling you this because of a number.
Mercer’s Global Talent Trends 2026 report found that 99% of the C-suite leaders it surveyed expect AI to drive at least some headcount reduction within two years. At least some. Read that part twice. Oliver Wyman and the New York Stock Exchange found something narrower. They surveyed 415 CEOs this spring, and 43% said they plan to deprioritize hiring for junior roles within the next year, up from 17% last year.
Junior roles are the media plans. They’re the repetitive spreadsheet nobody planned to teach you anything with.
So here’s the question I can’t get around. If software had made my media plans in 2007, would I have learned Excel? I don’t know. Probably not.
The boring work was the apprenticeship, and nobody called it that.
I don’t want to oversell it. It was my first job out of college and I was exhausted. I worked 40 to 50 hours a week at 22, and I partied most nights, either with work or with friends. We drank a lot in those days. I liked it and I hated it. And I got really good at the work and the economy cut me anyway.
The job also reached me through a person. It was offered to a friend first. He turned it down and recommended me.
I build with these tools. I’m the one telling you how fast this can go, so don’t read this as a warning from outside the building.
If a 22-year-old asked me what to do, this is what I’d say.
Stop worrying about not knowing everything. Be nice, and make as many friends as you can.
I can’t promise your career will get easier. I can promise you’ll get better, and you will get better at it.
Oh, and make a budget by the end of the week.